European Journal of Chemistry

Synthesis, antimicrobial, and antitubercular evaluation of new Schiff bases with in silico ADMET and molecular docking studies

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Published: Mar 31, 2022
DOI: https://doi.org/10.5155/eurjchem.13.1.109-116.2216
Keywords:
5V3Y, MABA, In silico, Antifungal activity, Multistep synthesis, Antibacterial activity
Section
Research Article
Issue
Vol. 13 No. 1 (2022): March 2022
Dates
Received 2021-11-18
Accepted 2022-01-03
Published 2022-03-31
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Sakshith Raghavendra Prasad
Department of Pharmaceutical Chemistry, National College of Pharmacy, Balaraj Urs Road, Shivamogga-577201, Karnataka, India
https://orcid.org/0000-0003-4700-1679
Nayak Devappa Satyanarayan
Department of Pharmaceutical Chemistry, Kuvempu University, Post-Graduate Centre, Kadur-577548, Karnataka, India
https://orcid.org/0000-0003-4511-3749
Avarse Satish Kumar Shetty
Department of Pharmaceutical Chemistry, National College of Pharmacy, Balaraj Urs Road, Shivamogga-577201, Karnataka, India
https://orcid.org/0000-0003-2903-7678
Basaiah Thippeswamy
Department of Post-Graduation Studies and Research in Microbiology, Jnanasahyadri, Kuvempu University, Shankaraghatta-577451, India
https://orcid.org/0000-0002-6436-0289

Abstract

Schiff bases are a proven moiety in antitubercular drug discovery and the antitubercular drug development. Drug discovery is a never-ending process due to evolving drug resistance by the bacteria, as a result, there is a need of developing new antitubercular drugs. In this continuous process of antitubercular drug discovery, new series of Schiff bases are synthesized using quinoline carbohydrazide upon coupling with different aldehydes in ethanolic media through multistep synthesis. These synthesized compounds were purified and characterized by different spectroscopic techniques. The molecules were in vitro screened for antifungal and antibacterial potential by Agar well diffusion assay, antitubercular activity by using microplate Alamar blue assay, and an attempt has been made to study the in-silico relationship between new Schiff base derivatives 4a-f and the crystal structure of M. tuberculosis (5V3Y) protein by molecular docking studies. Synthesized compounds 4a-f show good interaction with the crystal structure of M. tuberculosis protein (5V3Y) and fulfill ADMET characteristics in silico experiments. Among the compounds tested, compound 4d was found to be active against bacteria and fungi. Compound 4b was found to be sensitive against M. tuberculosis at 50 µg/mL concentration.


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Prasad, S. R.; Satyanarayan, N. D.; Shetty, A. S. K.; Thippeswamy, B. Synthesis, Antimicrobial, and Antitubercular Evaluation of New Schiff Bases With in Silico ADMET and Molecular Docking Studies. Eur. J. Chem. 2022, 13, 109-116.

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References

[1]. Alsayed, S. S. R.; Lun, S.; Bailey, A. W.; Suri, A.; Huang, C.-C.; Mocerino, M.; Payne, A.; Sredni, S. T.; Bishai, W. R.; Gunosewoyo, H. Design, synthesis and evaluation of novel indole-2-carboxamides for growth inhibition of Mycobacterium tuberculosis and paediatric brain tumour cells. RSC Adv. 2021, 11, 15497-15511.
https://doi.org/10.1039/D0RA10728J

[2]. Dheda, K.; Gumbo, T.; Maartens, G.; Dooley, K. E.; McNerney, R.; Murray, M.; Furin, J.; Nardell, E. A.; London, L.; Lessem, E.; Theron, G.; van Helden, P.; Niemann, S.; Merker, M.; Dowdy, D.; Van Rie, A.; Siu, G. K. H.; Pasipanodya, J. G.; Rodrigues, C.; Clark, T. G.; Sirgel, F. A.; Esmail, A.; Lin, H.-H.; Atre, S. R.; Schaaf, H. S.; Chang, K. C.; Lange, C.; Nahid, P.; Udwadia, Z. F.; Horsburgh, C. R., Jr; Churchyard, G. J.; Menzies, D.; Hesseling, A. C.; Nuermberger, E.; McIlleron, H.; Fennelly, K. P.; Goemaere, E.; Jaramillo, E.; Low, M.; Jara, C. M.; Padayatchi, N.; Warren, R. M. The epidemiology, pathogenesis, transmission, diagnosis, and management of multidrug-resistant, extensively drug-resistant, and incurable tuberculosis. Lancet Respir. Med. 2017, 5 (4), 291-360.
https://doi.org/10.1016/S2213-2600(17)30079-6

[3]. Schiff, H. Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen. Ann. Chem. Pharm. 1864, 131, 118-119.
https://doi.org/10.1002/jlac.18641310113

[4]. Bharti, S. K.; Nath, G.; Tilak, R.; Singh, S. K. Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring. Eur. J. Med. Chem. 2010, 45, 651-660.
https://doi.org/10.1016/j.ejmech.2009.11.008

[5]. Cordeiro, R.; Kachroo, M. Synthesis and biological evaluation of anti-tubercular activity of Schiff bases of 2-Amino thiazoles. Bioorg. Med. Chem. Lett. 2020, 30, 127655.
https://doi.org/10.1016/j.bmcl.2020.127655

[6]. Guo, S.; Song, Y.; Huang, Q.; Yuan, H.; Wan, B.; Wang, Y.; He, R.; Beconi, M. G.; Franzblau, S. G.; Kozikowski, A. P. Identification, synthesis, and pharmacological evaluation of tetrahydroindazole based ligands as novel antituberculosis agents. J. Med. Chem. 2010, 53, 649-659.
https://doi.org/10.1021/jm901235p

[7]. Santoshkumar, S.; Satyanarayana, N. D.; Anantacharya, R.; Sameer, P. Synthesis, antimicrobial, antitubercular and cheminformatic studies of 2-(1-benzofuran-2-yl)-N'-[(3Z)-2-oxo-1, 2-dihydro-3H-indol-3-ylidene] quinoline-4-carbohydrazide and its derivatives. Int. J. Pharm. Pharm. Sci. 2017, 9, 260-267.
https://doi.org/10.22159/ijpps.2017v9i5.17564

[8]. Kumar, S.; Bawa, S.; Gupta, H. Biological activities of quinoline derivatives. Mini Rev. Med. Chem. 2009, 9, 1648-1654.
https://doi.org/10.2174/138955709791012247

[9]. Tseng, C.-H.; Tung, C.-W.; Wu, C.-H.; Tzeng, C.-C.; Chen, Y.-H.; Hwang, T.-L.; Chen, Y.-L. Discovery of indeno[1,2-c]quinoline derivatives as potent dual antituberculosis and anti-inflammatory agents. Molecules 2017, 22, 1001.
https://doi.org/10.3390/molecules22061001

[10]. Gaber, A.; Alsanie, W. F.; Alhomrani, M.; Alamri, A. S.; El-Deen, I. M.; Refat, M. S. Synthesis of 1-[(Aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid Derivatives and Their Breast Anticancer Activity. Crystals (Basel) 2021, 11, 571.
https://doi.org/10.3390/cryst11050571

[11]. Salve, P. S.; Alegaon, S. G.; Sriram, D. Three-component, one-pot synthesis of anthranilamide Schiff bases bearing 4-aminoquinoline moiety as Mycobacterium tuberculosis gyrase inhibitors. Bioorg. Med. Chem. Lett. 2017, 27, 1859-1866.
https://doi.org/10.1016/j.bmcl.2017.02.031

[12]. Hunter, A. D. ACD/ChemSketch 1.0 (freeware); ACD/ChemSketch 2.0 and its Tautomers, Dictionary, and 3D Plug-ins; ACD/HNMR 2.0; ACD/CNMR 2.0. J. Chem. Educ. 1997, 74, 905.
https://doi.org/10.1021/ed074p905

[13]. Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. UCSF Chimera--a visualization system for exploratory research and analysis. J. Comput. Chem. 2004, 25, 1605-1612.
https://doi.org/10.1002/jcc.20084

[14]. Dallakyan, S.; Olson, A. J. Small-molecule library screening by docking with PyRx. Methods Mol. Biol. 2015, 1263, 243-250.
https://doi.org/10.1007/978-1-4939-2269-7_19

[15]. Kemmish, H.; Fasnacht, M.; Yan, L. Fully automated antibody structure prediction using BIOVIA tools: Validation study. PLoS One 2017, 12, e0177923.
https://doi.org/10.1371/journal.pone.0177923

[16]. Harishkumar, S.; Satyanarayan, N. D.; Santhosha, S. M. Antiproliferative and in silico admet study of new 4-(piperidin-1-ylmethyl)-2- (thiophen-2-yl) quinoline analogues. Asian J. Pharm. Clin. Res. 2018, 11, 306-313.
https://doi.org/10.22159/ajpcr.2018.v11i4.24147

[17]. Aggarwal, A.; Parai, M. K.; Shetty, N.; Wallis, D.; Woolhiser, L.; Hastings, C.; Dutta, N. K.; Galaviz, S.; Dhakal, R. C.; Shrestha, R.; Wakabayashi, S.; Walpole, C.; Matthews, D.; Floyd, D.; Scullion, P.; Riley, J.; Epemolu, O.; Norval, S.; Snavely, T.; Robertson, G. T.; Rubin, E. J.; Ioerger, T. R.; Sirgel, F. A.; van der Merwe, R.; van Helden, P. D.; Keller, P.; Böttger, E. C.; Karakousis, P. C.; Lenaerts, A. J.; Sacchettini, J. C. Development of a Novel Lead that Targets M. tuberculosis Polyketide Synthase 13. Cell 2017, 170, 249-259.e25.
https://doi.org/10.1016/j.cell.2017.06.025

[18]. PyMOL. The PyMOL Molecular Graphics System, Version 2.0 Schrödinger, LLC. http://www.pymol.org/pymol (accessed January 2, 2022).

[19]. Gaillard, T. Evaluation of AutoDock and AutoDock Vina on the CASF-2013 benchmark. J. Chem. Inf. Model. 2018, 58, 1697-1706.
https://doi.org/10.1021/acs.jcim.8b00312

[20]. Cheng, F.; Li, W.; Zhou, Y.; Shen, J.; Wu, Z.; Liu, G.; Lee, P. W.; Tang, Y. admetSAR: a comprehensive source and free tool for assessment of chemical ADMET properties. J. Chem. Inf. Model. 2012, 52, 3099-3105.
https://doi.org/10.1021/ci300367a

[21]. Lin, J. H.; Yamazaki, M. Role of P-glycoprotein in pharmacokinetics: clinical implications: Clinical implications. Clin. Pharmacokinet. 2003, 42, 59-98.
https://doi.org/10.2165/00003088-200342010-00003

[22]. Arthington-Skaggs, B. A.; Motley, M.; Warnock, D. W.; Morrison, C. J. Comparative evaluation of PASCO and national committee for clinical laboratory standards M27-A broth microdilution methods for antifungal drug susceptibility testing of yeasts. J. Clin. Microbiol. 2000, 38, 2254-2260.
https://doi.org/10.1128/JCM.38.6.2254-2260.2000

[23]. Rocha, L.; Marston, A.; Potterat, O.; Kaplan, M. A.; Stoeckli-Evans, H.; Hostettmann, K. Antibacterial phloroglucinols and flavonoids from Hypericum brasiliense. Phytochemistry 1995, 40, 1447-1452.
https://doi.org/10.1016/0031-9422(95)00507-4

[24]. MacLowry, J. D.; Jaqua, M. J.; Selepak, S. T. Detailed methodology and implementation of a semiautomated serial dilution microtechnique for antimicrobial susceptibility testing. Appl. Microbiol. 1970, 20, 46-53.
https://doi.org/10.1128/am.20.1.46-53.1970

[25]. Portillo, A.; Vila, R.; Freixa, B.; Adzet, T.; Cañigueral, S. Antifungal activity of Paraguayan plants used in traditional medicine. J. Ethnopharmacol. 2001, 76, 93-98.
https://doi.org/10.1016/S0378-8741(01)00214-8

[26]. Maria, C. S. L.; Marcus, V. N.; de Souza. Alessandra, C. P.; Marcelle de, L. F.; Raoni S. B. G.; Thais Cristina, M. N.; Monica, A. P. Evaluation of anti-tubercular activity of nicotinic and isoniazid analogues. ARKIVOC 2007, 2007, 181-191.
https://doi.org/10.3998/ark.5550190.0008.f18

[27]. Lipinski, C. A. Lead- and drug-like compounds: the rule-of-five revolution. Drug Discov. Today Technol. 2004, 1, 337-341.
https://doi.org/10.1016/j.ddtec.2004.11.007

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Kuvempu University, Shankaraghatta-577451, India.
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